7-(3-(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)propoxy)-3-methyl-3,4-dihydroquinolin-2(1H)-one | 1401333-14-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-(3-(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)propoxy)-3-methyl-3,4-dihydroquinolin-2(1H)-one
• 英文别名: (±)-SIPI 6360；7-[3-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]propoxy]-3-methyl-3,4-dihydro-1H-quinolin-2-one
• CAS: 1401333-14-9
• 化学式: C₂₅H₂₈FN₃O₃
• 分子量: 437.514
• InChiKey: VNARHBGTWQXKOB-UHFFFAOYSA-N

物化性质

• 沸点：
  646.6±55.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  67.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-氟-3-哌啶-4-基-1,2-苯并异唑盐酸盐 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 potassium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 7-(3-(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)propoxy)-3-methyl-3,4-dihydroquinolin-2(1H)-one
  参考文献：
  名称：

  Development and Kilogram-Scale Synthesis of a D₂/5-HT_2A Receptor Dual Antagonist (±)-SIPI 6360

  摘要：

  The kilogram-scale synthesis of a D-2/5-HT2A receptor dual antagonist (+/-)-SIPI 6360 was developed as an alternative treatment for schizophrenia. Specifically, three conditions were modified and optimized, including the Vilsmeier conditions, to prepare quinoline 3. In addition, the palladium-catalyzed hydrogenation was modified to synthesize dihydroquinolin-2(1H)-one 5, and the reduction of beta-chloroamide was altered to form 3-chloropropanamine 8. Ultimately these improvements led to the preparation of a 1.5 kg of (+/-)-SIPI 6360 batch in eight steps with an overall yield of 34% and purity of 99.8%.

  DOI：

  10.1021/acs.oprd.6b00220

文献信息

• Development and Kilogram-Scale Synthesis of a D₂/5-HT_2A Receptor Dual Antagonist (±)-SIPI 6360
  作者：Xiao-Wen Chen、Yu Liu、Xun-Qi Jin、Yuan-Yuan Sun、Shun-Lin Gu、Lei Fu、Jian-Qi Li

  DOI：10.1021/acs.oprd.6b00220

  日期：2016.9.16

  The kilogram-scale synthesis of a D-2/5-HT2A receptor dual antagonist (+/-)-SIPI 6360 was developed as an alternative treatment for schizophrenia. Specifically, three conditions were modified and optimized, including the Vilsmeier conditions, to prepare quinoline 3. In addition, the palladium-catalyzed hydrogenation was modified to synthesize dihydroquinolin-2(1H)-one 5, and the reduction of beta-chloroamide was altered to form 3-chloropropanamine 8. Ultimately these improvements led to the preparation of a 1.5 kg of (+/-)-SIPI 6360 batch in eight steps with an overall yield of 34% and purity of 99.8%.